


Five Things Dean Did While Sam Was At Stanford That He Probably Shouldn't Have

by icebucky



Category: Supernatural
Genre: Destiel - Freeform, F/M, Flashbacks, M/M, Male escort dean, Oprah, Stripper Dean, Tattoo, Truth or Dare, embarrassing stories
Language: English
Status: In-Progress
Published: 2014-10-07
Updated: 2014-10-08
Packaged: 2018-02-20 07:39:59
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 2,640
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2420534
Author URL: https://archiveofourown.org/users/icebucky/pseuds/icebucky
Summary: <blockquote class="userstuff">
              <p>No one knows what Dean got up to in the year and a half between Sam's departure for Stanford and Dean's return to hunting with John.</p>
<p>No one except Dean, that is. And he doesn't seem to be telling.</p>
<p>But with time to kill in the car, Sam decides to get the truth out of his brother, and with a little help from Cas, they might actually uncover five things about Dean that neither of them had known before, but that they really shouldn't have been surprised about.</p>
            </blockquote>





	1. An Introduction

**Author's Note:**

  * For [suckmycas](https://archiveofourown.org/users/suckmycas/gifts).



No one knew what Dean had been up to in the time that Sam had gone to Stanford and their family had fallen apart. He'd left, not explaining to his dad why he had to get out, never telling anyone where he'd disappeared to, taking the Impala and gunning the engine.

John remembered his oldest son, his firstborn, speeding off on the highway away from him, in the car that had practically been their house since he was four years old, and he didn't look back.

He left his father standing alone on the side of the road, his truck parked in a little dirt clearing off the side of the road, and he didn't look back.

Dean didn't explain why he'd left. He didn't offer any explanation when he came back a year and a half later, he just shrugged off his father's questions and pretended not to hear the urgency in his tone, but in all honesty, Dean didn't want to answer because he wanted there to be a teeny portion of his life that his father had absolutely no control over.

John couldn't make Dean tell him what he'd done or where he'd gone; there was a year and a half of his life locked away that he didn't intend to tell anyone about. It's not like they'd understand anyway, but even if they did and even if they asked, he still wouldn't explain.

Sam never asked. Dean was sure that he hadn't even noticed or entertained the possibility that when he left that his older brother would leave too. Dean knew how Sam saw him; he was a soldier, a mindless drone, a slave to his father's will who didn't know any answer other than _yes sir_. When the search for John brought them together again, they didn't talk about their pasts, but Dean would be lying even more than ordinary if he said that this didn't matter to him.

Maybe this was because Sam was the only reason he really had for leaving. Sam was gone, so he didn't have a reason to stay. Sammy had been his mission for as long as he could remember, the constant mantra of watch out for Sammy a thrumming through his head. He couldn't not watch out for Sammy, and when there was no Sammy to watch out for, he didn't quite know what to do with himself.

Dean didn't know what to do with himself, so he drove.

He didn't know what direction to go, just that he had to go in the opposite direction that Sam had gone. Sam didn't want them, Dean wouldn't give him the satisfaction of knowing that it was almost as though his brother had followed him.

It wasn't like Sam would know he had left Dad anyway, but that was besides the point.

He made a name for himself in a community that he was sure would earn him endless teasing from Sam and overbearing disapproval from John, but he was happy, and that was all that really mattered to him.

He put his guns back in the trunk and locked the fake door, and he thought for half a second that maybe he could throw away the key, forget about everything that had happened for his entire childhood, but Dean wasn't an idiot, and he knew that even if he got rid of the reminder, the universe has a way of picking the lock anyway.

The year and a half that Dean took from hunting was a bubble that he locked away, a sacred knot of time that he would not, could not, desecrate by speaking about it in his normal life.

Not that Sam ever asked, but he couldn't talk about it. He wouldn't. Because he had a list of things that he did in that time period that he probably shouldn't have, but he didn't regret it for the world.


	2. The Rainbow

"So, Dean," Sam said conversationally from the passenger seat, "truth or dare?"

Dean cut his brother a glance, looking away from the road for a second too long to be safe. "What the hell are you talking about?"

Sam shrugged. "I dunno, it's not like we have anything better to do. I mean, we already went over the job and I'm sick of sleeping and avoiding talking about family shit."

"Why the hell truth or dare?" Dean asked sharply, tensing at Sam's explanations. "We've never played truth or dare before."

"Ex _act_ ly," Sam replied, punctuating his emphasis by poking the pen he'd been tapping against his teeth in Dean's general direction. "We've never played truth or dare. What kind of brothers are we, man?"

"Truth or dare is overrated, Sammy," Dean said, flicking his eyes up to the rear view mirror and cursing softly at the pickup truck on his ass. "And anyway, all the options are the fuckin' same all the time anyway. I mean, come on, it's pretty much a) perform some strange sexual and/or illegal act or b) tell me who you like." Sam snorted, and Dean rolled his eyes. "You know who makes other people play games like that? Vultures. You're a fuckin' vulture, Sam."

"Dean," his brother sighed, looking out of the window. "I'm just trying to pass the time."

Dean opened his mouth to retort sharply, but a gravelly voice from the backseat interjected, "I think it's a good idea."

Dean turned so quickly that the car jerked a little in the lane, and through Sam's gasp of "Dean, watch the road!" he caught a glimpse of a messy head of dark hair and a tan trench coat. "Damn it, Cas, don't do that when I'm driving!"

"My apologies," the angel replied serenely. "Hello, Dean. Sam."

"Hey, Cas," Sam breathed, focused on Dean's driving. "You need me to drive? You've been going for five hours already."

"Shut up. I got it," Dean growled, and Sam sighed heavily.

A moment of glorious silence, broken only by the sounds of Zeppelin, and then - "Truth or dare, Cas?"

"Oh my god, Sam, will you drop it?" Dean nearly shouted, and Sam's eyes darted to him, widened slightly in surprise.

"Dude, calm down. I asked Cas, not you. And what the fuck do you have against truth or dare anyway?"

"Not all of us got to play it with our college friends, Sammy," Dean snarked, but fell silent at the warning look he got from Cas in the rear view mirror. He reluctantly dropped his eyes back to the road.

"Um," Cas said, his voice seeming to wander through the car, "truth, I suppose."

Sam didn't hesitate. "Do you have a crush on Dean?"

Dean nearly sent the car spinning into another lane again, his hands jerking, and as he glanced up in the rear view mirror, he saw that Cas' cheeks were tinged pink. "Yo, Sammy, you can't ask the heavy questions this early in the game. That ain't how it works."

Sam scoffed. "Someone's avoiding the question and the possible answer, okay then. Fine. How about... Have you ever read fanfiction about the Supernatural books?"

"We all have, Sam. Don't ask stupid questions," Castiel replied briskly, and Sam laughed.

"Your turn, Dean," he continued, directing his attention to the older Winchester, and Sam sat up eagerly. "Truth or dare?"

"Dare," he replied with certainty. "I'm not a wuss."

Sam snorted. "Yeah, but you're an idiot." He began tapping the pen against his teeth again, looking out of the window. "I got it. I dare you," he dragged out the word, clicking the pen sharply and cutting his attention back to his brother. "I dare you to... um, sing a High School Musical song at the next karaoke bar we go to."

"We can't do that from the highway, Sammy, you gotta pick something less stupid. Truth."

Sam grinned, glancing back at Cas. "Okay. Fine, then. What's the story behind the weird ass rainbow tattoo on your left hip?"

"Yes, how did you get the rainbow tattoo?" Castiel cut in sharply, in roughly the same tone of horror and surprise he'd expressed when he asked _you have a dungeon?_ Same thing. The brothers mostly ignored him.

Dean sighed heavily. "Damn it, Sammy, you really gonna do this?"

"Yeah," Sam answered, like it was obvious. "You won't tell me, so I charge you under penalty of truth or dare to answer. Why the hell do you have a rainbow tattoo on your left hip?"

"Well, long story short, I went to a bar and I got drunk and I got some ink."

"No!" Sam nearly shouted, and Dean jumped a little. "That is _not_ the whole story, jerk! You have to tell the whole story and the whole _true_ story."

"Fuck you, Sam," Dean growled, and Sam laughed. "Fine. Fine. Okay, here's the fucking story. Lemme see, I think it was... June, 2001."

Sam had been gone for a few weeks, and it was too quiet in the motel rooms. Dean never really told his father that he was leaving, he just pulled to the side of the road one day and pretended not to notice the look of hurt on John's face.

"I need a break, Dad," he said, looking at his hands on the roof of the Impala. "I can't keep doing this without Sammy. Not yet."

"Okay," John had quietly replied, reaching out and clapping his son on the shoulder. "Be safe, son."

In retrospect, Dean was surprised that his dad hadn't tried to stop him at all, but he reasoned that it was because he knew that he was coming back.

It almost bothered him how certain John was in that thought, but Dean didn't really have a reason to object; he was coming back, after all.

Dean didn't have anywhere to go, so he drove. It was almost mindless, picking a random exit and swinging into a city buried somewhere in the Midwest that had a surprisingly impressive night life.

He had essentially lost his family, but this time it was his choice, so what other course of action would he take other than going and getting totally smashed in the first fun looking bar he came across? He was twenty-two, he didn't even have a need for a fake ID anymore.

About halfway into his fourth shot with a nameless blonde who kept giggling and smelled like cigarette smoke, Dean picked up on the fact that this was a college town.

Fan-fucking-tastic.

Somewhere along the line, he ended up lounging on a couch with a bunch of other drunk people. He must have really liked them at one point, for him to agree when one girl excitedly slurred that they should get tattoos.

Thirty minutes later, after stumbling in and leaning on each other's shoulders, Dean stared up at the past designs trying to choose what to get, but his brain wasn't working right, he couldn't focus long enough to remember what he was doing. Tattoo. It was cool, right? It's not like he could afford it, but who gives a shit, it's college, no one can afford anything anyway.

He didn't remember that he wasn't actually in college until the guy who came out to ink up the first of his party friends said his name was Sam.

"Fuck," Dean hissed under his breath and the clingy brunette that he had his arm wrapped around patted his chest and looked up at him in vague concern.

"What's wrong, Deanie?" she asked, and he couldn't answer, he shouldn't have had this much to drink, but too late now, he just had to try and not let his eyes show that he missed his little brother and that's why he was in a tattoo parlor pretending he wanted one of these things.

What did he want? Not just now, in this moment, but this was an existential crisis if Dean had ever had one. He never knew what he wanted, he just knew what he'd had to do. Fuck. He was on his own now, and he was going to get a reminder of it. Screw Dad, and screw Sam. They made their choices, they never cared what Dean wanted.

"Hey, babe, pick something for me," he said to the girl, and she giggled and went off to whisper something to one of the artists.

In all honesty, Dean didn't remember anything much about the rest of the night. He did remember, however, waking up with a pounding headache, his legs tangled with those belonging to a girl that he didn't recognize, and a burning sensation on the skin of his left hip.

"And that, boys, is what happens when you let a drunk girl pick your tattoo for you," Dean finished, signaling at the last minute to swerve onto an exit. "Lunch time. Everybody get out," he added, pulling into a parking lot of a fast food joint.

Sam was laughing, shaking his head as he got out of the car, coming around the front to get to the door of the restaurant. "Hey, before we go in, can I see it again?"

Dean scowled. "Hell no, bitch. What the fuck makes you think I'd show you that thing?"

Sam would have made a more convincing argument if he hadn't been nearly crying with laughter, but he managed to choke out, "Cas - Cas still hasn't seen it."

Dean could tell that Cas, who had remained silent during his story, while Sam had been laughing and trying to interrupt (and while Sam's laughter had admittedly been nice to hear for once, it was still irritating as hell), had walked up to stand at around his shoulder. "You wanna see my ink, Cas?" Dean asked harshly, and Cas shrugged.

"I reassembled every part of your body when I raised you from hell, Dean. You think I don't know what the rainbow tattoo looks like?"

Unless Sam's eyes were cloudy from the tears of laughter, he could swear that Dean had dropped his gaze a little, cheeks flushed, and he was biting his lower lip delicately.

"Well, I just -" he stopped and cleared his throat. "- I don't know, I thought it was a trust thing. All that shit."

"I suppose so," Castiel replied, and he and Dean stared at each other for perhaps a bit more than strictly necessary before Dean lifted up his shirt at his left hip and yanked down the waistband of his boxers a little bit to reveal the tattoo.

Sam had never really gotten a good look at it until this moment, and he saw that not only was it a delicately inked rainbow, it also said _follow your dreams_ in flowing script around the top.

"Yeah, yeah, I know," Dean said, attempting to brush off any criticism, but Sam didn't hear him. He had to leave to preserve a little of his dignity before he collapsed and possibly pissed himself from laughter.

But the thing is, if he hadn't left, he wouldn't have missed the tender way that Cas touched Dean's hip, lightly brushing the rainbow with his fingers, and how Dean dropped his shirt, eyes slightly glazed, and exactly how long they stared at each other (Dean licking his lips nervously, Cas' eyes following his movements) before he reappeared, breaking the contact.

Sam had an uncanny knack of walking in or out at exactly the wrong moments, and this was one of both of them, but that's a different story.

Dean and Cas put a considerable distance between them and followed Sam into the restaurant, noticeably trying not to touch or interact accidentally. "Don't think the game is over though," Sam called back, not missing the way that their heads swiveled to each other. "Dean, you pick the next person."

Dean grinned, and Sam had the sinking feeling that he'd made a fatal mistake.


End file.
